The HŪMNZ Element: Issue 34 - The Hire Every CEO Delays Too Long

The signal most owners wait for is the feeling of being overwhelmed, and it arrives about two years late. The structural signals are visible long before it.

Author

Tim Dennis
October 06, 2026

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💡 Editor's Note

Most owners hire a second-in-command about two years after they needed one.

Not because they cannot afford it. Because the signal they are waiting for is the feeling of being overwhelmed, and that feeling shows up late, reads as a personal shortcoming, and responds to working harder — which postpones it again.

The better signals are structural, and they are visible long before the feeling arrives.

This week is about what those signals are, what the role is actually for, and what has to leave your desk for it to work.

Find out which parts of your operation still run through you.

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Executive Brief

Bottom line: A second-in-command fails far more often from a vague brief than from a bad hire, and the brief is vague because the owner never wrote down what the role is for.

There is a tidy story about this decision: the company grows, the founder gets stretched, a capable deputy arrives, things improve. It rarely runs that way.

What usually happens is that an owner reaches the end of their capacity, hires someone experienced and well-regarded, hands over a collection of things they personally dislike doing, and discovers eighteen months later that the work came back. Both people are competent. The arrangement still did not hold.

The reason is almost always the same. Nobody decided, in one sentence, what the role existed to do — so the owner kept the decisions, the deputy inherited the tasks, and the company gained an expensive coordinator.

In 30 seconds

  • Waiting until you feel overwhelmed means hiring late. The useful signals are structural — work queued behind your decisions, functions reporting to you out of habit, relationships only you hold.

  • Write one sentence finishing "we are creating this role so that..." before you write a job description. If it takes a list to complete, the role is not defined yet.

  • Name three decisions that belong to the deputy alone from day one, and tell the team. Authority that is never transferred is the most common way this hire fails.

⚠️ Four signals leaders should be watching this week

1. What is the role actually for?

Signal: The decision gets made as "I need help," which is a feeling rather than a job description.

Evidence: Nate Bennett and Stephen Miles, writing in Harvard Business Review in 2006, identified seven genuinely different reasons companies create a second-in-command role: to execute the chief executive's strategy, to lead a particular initiative such as a turnaround, to mentor an inexperienced CEO, to offset the chief executive's own weaknesses, to act as a partner, to test a potential successor, or to keep a valuable executive a competitor was circling. Their argument is that the role underperforms mainly because the motive behind it is never stated, and each of those motives describes a different job.

Implication: Two people can agree completely that the company needs a number two and still be describing two different hires. One of them is a successor. Another is a fixer. A third is a partner. They are not interchangeable, and the gap only becomes visible after someone has started.

Action: Finish this sentence before writing anything else: "We are creating this role so that ___." If you cannot complete it without listing three things, you are not ready to hire yet.

2. Which signals say you have already waited too long?

Signal: Owners wait for a feeling, and the feeling is a lagging indicator of a structural problem.

Evidence: The Bridgespan Group's field research on how these roles get built describes the position as one that is created, shaped, and sometimes removed to suit an organization at a particular point in its development. In other words it is a decision about the stage the company has reached, not about the stamina of the person running it.

Implication: Treating it as a stamina question makes it a referendum on you, which is exactly why it gets deferred. Treating it as a stage question makes it an ordinary design decision with an ordinary answer.

Action: Four questions, and you can answer all of them today. What has been sitting waiting on your decision for more than a week? Which functions report to you only because they always have? What would stall first if you were unreachable for a month? Who holds the relationships you would have to hand over personally? Anything you cannot answer comfortably is the argument.

3. What do you actually have to give up?

Signal: The title gets transferred on day one. The authority never does.

Evidence: Bennett and Miles are specific about what the arrangement asks of the chief executive, not just the deputy. The CEO has to communicate openly, grant genuine decision-making power, and avoid undercutting the deputy's standing in front of the organization. They describe trust between the two as the binding constraint on whether the role works at all.

Implication: Most disappointing second-in-command hires are not hiring failures. They are delegation failures wearing a hiring failure's clothes. You can choose exactly the right person and still make the job impossible by keeping the final word on everything that matters.

Action: Before they start, name three decisions that will be theirs alone, write them down, and say so to the team. Then leave those three alone for a quarter, including the times you would have decided differently.

4. What shape should the role take?

Signal: The role gets copied from another company, where it solved a different problem.

Evidence: Bridgespan's research describes three shapes that recur. In the first, the deputy takes operations and administration while others keep delivery. In the second, the deputy takes delivery while the chief executive keeps administration. In the third, the deputy takes everything internal so the chief executive can work almost entirely outside the business.

Implication: None of the three is correct in general. The right one depends on which half of the job you are genuinely better at, and which half you should still be doing in two years.

Action: List the things you would keep even if you had a perfect deputy tomorrow. That list is the shape of the role, and it is a more honest starting point than any job description you could borrow.

Worth Knowing

The seat has a daily cost

Gallup's April 2026 analysis of 9,880 people who manage other managers found them more likely than individual contributors to report having felt anger the previous day — 33% against 21% — along with higher stress and loneliness.

That is a finding about senior roles generally, not about missing a deputy. It is worth sitting with anyway. The cost of the seat is real and measurable, and every function that still reports to you is added to it.

Sources: Nate Bennett and Stephen A. Miles, "Second in Command: The Misunderstood Role of the Chief Operating Officer," Harvard Business Review, May 2006. The Bridgespan Group, "COO Roles and Structures: Stories from the Field." Gallup, "Leaders Have Better Lives but Worse Days," April 8, 2026.

The Core Question

There is a version of this hire that changes nothing. The deputy arrives, takes over the parts of the week you liked least, and becomes very good at bringing you decisions. Your calendar looks different. Your week does not.

The version that works is uncomfortable in a specific way: things get decided that you would have decided differently, and you find out afterwards.

If this person started on Monday, what would actually leave my desk — and stay gone?

The VALŪE lens: A company where every real decision routes through one person is slower to run and worth less to anyone else. A second-in-command is the point at which an owner-operated business becomes an operating company, which is a change in what the business is, not only in how the week feels.

The hire is not the hard part. Letting it work is.

Know a CEO who has been meaning to make this hire for a year? Send it on.

Until next time,

The HŪMNZ Element — Weekly Pulse

If this was useful, forward it to one person: a CEO who cannot take a clear week off, or whoever would have to cover for them.